2-Chloro-6-methylbenzoyl chloride → 2-Chloro-N-ethyl-6-methyl-N-[3,3,3-trifluoro-2-({[1-(4-fluorophenyl)-1H-indazol-4-yl]amino}methyl)-2-hydroxypropyl]benzamide

HRID 551487Notes

Reaction equation

HRID 551487 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4](Cl)=[O:5].[F:12][C:13]([F:40])([F:39])[C:14]([CH2:34][NH:35][CH2:36][CH2:37]C)([OH:33])[CH2:15][NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[N:20][N:21]2[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([N:35]([CH2:36][CH3:37])[CH2:34][C:14]([CH2:15][NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[N:20][N:21]2[C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)([OH:33])[C:13]([F:12])([F:40])[F:39])=[O:5]

Participants

4

Reactant 2

HCID 223820402-Chloro-6-methylbenzoyl chlorideHCID 59324137HCID 59324137, compound

Product 1

HCID 593241222-Chloro-N-ethyl-6-methyl-N-[3,3,3-trifluoro-2-({[1-(4-fluorophenyl)-1H-indazol-4-yl]amino}methyl)-2-hydroxypropyl]benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared similarly to Example 48 by reaction of 2-chloro-6-methylbenzoylchloride and 1,1,1-trifluoro-3-{[1-(4-fluorophenyl)-1H-indazol-4-yl]amino}-2-[(propylamino)methyl]-2-propanol in chloroform over 42 hours. Purification by mass directed autopreparation (System B) resulted in separation of atropisomers of the title compound:

Workup

  1. customPurification by mass

Sources & evidence

ORD record
ord-a3ee8940c0174d59a04173ccd8e5eb8e
Source dataset
uspto-grants-2011_05
Patent number
US07947727B2

Reaction notes

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